My family and I are completely on board for an owner occupied/house hack option, however I see this could be challenging, being the landlord downstairs or next door with 3 screaming children; banging on walls and the likes as most children do.

I wanted quality cabinets, and wasn't interested in particle boards. 

You will have to get the alderman on board (politics..) and then the neighbors about hours and parking..It's a cool project, it feels like you make an impact on the community, but I would only do that if I had too much money, nothing to do with my time and looking for a proper challenge.

No need to worry about crappy particle or press board problems, as they are plywood construction.

You can always ask for a tax recert and challenge the assessment file a petition to the VAB value adjustment board and dispute assessment.If all of that fails start looking at investment properties in states like TN, LA, AL, GA, FL, these states in the South East can offer super low annual property taxes. 

Here's a PARTIAL list:Office rentComputers, printers & softwareInternet & phone billOffice furnitureOffice supplies: paper, postage, ink, etc.Office liability insuranceAuto expenses: monthly payment, insurance, gas, maintenance, registration/plate feesBroker license fees: annual, monthly board & MLS fees, continuing education fees, E&O insuranceEquipment: lockboxes, signs, etc.Payroll & payroll taxesBusiness income tax preparation and paymentsLabor: answering phones, calling past due tenants, scheduling tours, taking marketing pics, processing those pics, writing ads, researching rent amounts, posting ads, explaining to owners how rent determined & showing where ad posted, opening & processing mail, posting payments, bank deposits, scanning documents & posting to owner & tenant portals, explaining accounting to owners so they understand their monthly statements, taking pics/videos of repairs, finding reputable handymen and contractors, confirming they're properly licensed & insured and tracking annually, verifying repairs done properly, processing invoices for utility bills, repairs, taxes, city inspections, scheduling periodic property evaluations/inspections with tenants that don't want strangers in their homes, explaining to owners why taking so long, and more & more & more...

My sister and father are lawyers and have fought their taxes all the way through the process and have gotten very little relief from the tax board.

You're throwing darts at a board with one eye closed hoping to get lucky. 

Hi Bob,Make sure to have an investor friendly realtor so that you won't have issues afterwards.HOA are very tricky, as the boards change very often, they could be years that they don't do much and other years that they are suing residents if they are not maintaining the lawn.CC&R are the key to review in this case, those are public so available for you, and those are required to be provided by the seller every time.Don't go the route of do it anyways, that will have cause you consequences, I had a time that the HOA sued a property owner just for missing 6 months (the property owner was renting out the property and it didn't receive the invoice to pay the dues so she forgot).

Bylaws and rules can often be changed by the Board (depending on what the higher documents require), while the CC&Rs and Incorporation docs are intended to be more difficult to change and often require a vote with a super majority of all owners to change.